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Showing Compound androst-4-en-3,17-dione (FDB030678)

Record Information
Version1.0
Creation date2015-05-07 19:46:52 UTC
Update date2019-11-26 03:21:51 UTC
Primary IDFDB030678
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameandrost-4-en-3,17-dione
DescriptionAndrost-4-en-3,17-dione, also known as androstenedione or delta(4)-androsten-3,17-dione, belongs to androgens and derivatives class of compounds. Those are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, androst-4-en-3,17-dione is considered to be a steroid lipid molecule. Androst-4-en-3,17-dione is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Androst-4-en-3,17-dione can be found in a number of food items such as naranjilla, purslane, common cabbage, and oval-leaf huckleberry, which makes androst-4-en-3,17-dione a potential biomarker for the consumption of these food products. Androst-4-en-3,17-dione can be found primarily in blood, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. In humans, androst-4-en-3,17-dione is involved in a couple of metabolic pathways, which include androgen and estrogen metabolism and androstenedione metabolism. Androst-4-en-3,17-dione is also involved in a couple of metabolic disorders, which include 17-beta hydroxysteroid dehydrogenase III deficiency and aromatase deficiency. Moreover, androst-4-en-3,17-dione is found to be associated with rheumatoid arthritis, thyroid cancer , cushing's Syndrome, and schizophrenia. Androst-4-en-3,17-dione is a non-carcinogenic (not listed by IARC) potentially toxic compound.
CAS Number63-05-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4-Androstene-3,17-dioneChEBI
4-ANDROSTENE-3-17-dioneChEBI
delta(4)-Androsten-3,17-dioneChEBI
delta(4)-Androstene-3,17-dioneChEBI
Δ(4)-Androsten-3,17-dioneGenerator
Δ(4)-Androstene-3,17-dioneGenerator
(4)-Androsten-3,17-dioneHMDB
17-KetotestosteroneHMDB
3,17-Dioxoandrost-4-eneHMDB
4-Androsten-3,17-dioneHMDB
4-AndrostenedioneHMDB
Androst-4-ene-3,17-dioneHMDB, KEGG
AndrostendioneHMDB
D4-Androstene-3,17-dioneHMDB
delta4-AndrostenedioneHMDB
FecundinHMDB
delta 4 AndrostenedioneMeSH, HMDB
delta-4-AndrostenedioneMeSH, HMDB
4 Androstene 3,17 dioneMeSH, HMDB
AndrostenedioneHMDB
delta4-Androstene-3,17-dioneHMDB
Δ4-Androstene-3,17-dioneHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP2.93ALOGPS
logP3.93ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)19.03ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.61 m³·mol⁻¹ChemAxon
Polarizability33.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H26O2
IUPAC name(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
InChI IdentifierInChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
InChI KeyAEMFNILZOJDQLW-QAGGRKNESA-N
Isomeric SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Average Molecular Weight286.4085
Monoisotopic Molecular Weight286.193280076
Classification
Description Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-059m-3940000000-9cb32ac21e46afb2829aSpectrum
GC-MSandrost-4-en-3,17-dione, non-derivatized, GC-MS Spectrumsplash10-004l-5910000000-518e1ad38bcc73325b53Spectrum
GC-MSandrost-4-en-3,17-dione, non-derivatized, GC-MS Spectrumsplash10-004l-5910000000-5172e05f9889ee2bfaf4Spectrum
GC-MSandrost-4-en-3,17-dione, non-derivatized, GC-MS Spectrumsplash10-000f-8940000000-f2892fe3b281d44164c8Spectrum
GC-MSandrost-4-en-3,17-dione, non-derivatized, GC-MS Spectrumsplash10-007d-1960000000-167f1765b095da9d603bSpectrum
GC-MSandrost-4-en-3,17-dione, non-derivatized, GC-MS Spectrumsplash10-004l-5910000000-518e1ad38bcc73325b53Spectrum
GC-MSandrost-4-en-3,17-dione, non-derivatized, GC-MS Spectrumsplash10-004l-5910000000-5172e05f9889ee2bfaf4Spectrum
Predicted GC-MSandrost-4-en-3,17-dione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-0590000000-502d6b821317a01a1990Spectrum
Predicted GC-MSandrost-4-en-3,17-dione, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-36e848ba16b141eef47bSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-9600000000-712954fc35a84c8217deSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9300000000-f8e9aa16b4b208b69f7bSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-000f-8940000000-e12025ea2b7808c64b9cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052b-6910000000-b616785c86a92f46158eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052b-9800000000-73e545a1eb2232d55371Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kb-5790000000-735473bc44dd70e29259Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kb-5790000000-114675a4457063901f2bSpectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-052b-7910000000-f0d8591998137c42f717Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00kb-5790000000-f47366cff1ef47253455Spectrum
MS/MSLC-MS/MS Spectrum - 80V, Positivesplash10-052b-9800000000-58ced8830fbdd255377eSpectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-00kb-5790000000-4d32bf4d34aaef92de91Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-052b-9700000000-5a645018a15e2dd1adebSpectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-052b-9500000000-70913f3a4e21abdcf9eeSpectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-052b-9500000000-1405c9c7f6ea07c8d1e4Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-eec15e6fd9d08b27ef07Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-778071650dcadc3b3069Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00c3-0900000000-faf22b1b9717d889edd8Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00ei-0940000000-930c091a3d1471221653Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-0347db9e9578e8d5d6f2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05pc-0490000000-d4049441f1c172450dc3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-4790000000-355bc0834a6465ecad30Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-887b6f223b77c683ef99Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-9dafdd780cca012f1fb3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-2190000000-264074b1eefeed0e3103Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference